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Organic chemistry is the branch of chemistry that deals with carbon compounds. But all carbon
compounds are not considered as organic compounds. (E.g. CO2, CO, metal carbonates, bicarbonates etc.). So
organic chemistry can be defined as the branch of chemistry that deals with hydrocarbons and their derivatives.
Hydrocarbons are the major class of organic compounds and they contain only carbon and hydrogen atoms. All
other organic compounds are formed by replacing one or more hydrogen atoms of hydrocarbons by other atoms
or groups (They are called hydrocarbon derivatives).
All carbon compounds present in plants and animals are organic compounds. E.g. Carbohydrates,
proteins, vitamins, nucleic acids, amino acids, fats and oils, natural polymers etc. petroleum and coal are the
major source of organic compounds (hydrocarbons).
In ancient times, it was believed that a vital force (living body) is necessary for the production of an
organic compound. But in 1828, Frederic Wohler proved that this belief was wrong. He prepared urea in the
laboratory, by heating ammonium cyanate (NH4CNO). It was the first organic compound prepared in the
laboratory.
NH4CNO Heat NH2CONH2
Ammonium cyanate Urea
Then another scientist Kolbe synthesized acetic acid and Berthelot synthesized methane in the
laboratory. Nowadays about 95% of the organic compounds are synthesized in the laboratory.
Chemistry behind the existance of large number Carbon compounds
Carbon is a unique element and it can form a large number of compounds due to the following reasons:
i) Tetravalency of carbon: In all of its compounds, the valency of carbon is four. Carbon has 4 electrons
in its valency shell and requires 4 more electrons to complete the octet. So it attains the octet
configuration by forming 4 covalent bonds.
ii) Ability to form single bond and multiple bonds: C can form single bond and multiple bond (double or
triple bond) with itself and also with other elements like oxygen, nitrogen etc. This is possible by sp3,
sp2 or sp hybridisation.
iii) Catenation: Carbon shows catenation. It is the self linking property of an element to form long chains
and rings.
iv) Isomerism: Carbon compounds can show isomerism. It is the phenomenon in which compounds
having same molecular formula but different structural formula or spatial arrangement of atoms.
Structural representation of organic compounds
An organic compound can be represented by the following ways:
1. Complete structural formula: Here all the bonds between atoms are denoted by dashes (----). A single
dash represents a single bond, a double dash represents a double bond and a triple dash represents a
triple bond. E.g.
2. Condensed stuctural formula: Here the carbon-hydrogen bonds or all the bonds are omitted except the
multiple bonds. It is a simplified representation of an organic compound.
E.g. ethane - CH3CH3, propane - CH3CH2CH3, butane - CH3CH2CH2CH3, ethene - CH2=CH2 etc.
XI Chemistry Notes By Anil Kumar K.L [HSSLiVE] Page 1
The condensed formula can again simplified as follows:
Butane CH3(CH2)2CH3, Hexane- CH3(CH2)4CH3, Decane CH3(CH2)8CH3 etc.
3. Bond line representation: It is the simplest form of representation of an organic compound. Here carbon
and hydrogen atoms are not shown and the lines representing carbon-carbon bonds are drawn in a zig-zag
fashion. The only atoms specifically written are oxygen, chlorine, nitrogen etc. The free terminals denote
methyl (CH3) groups.
E.g. butane:
3-methyl pentane:
Heptanal: H
O
3-Methyl pentanoic acid: OH
O
4. Three-Dimensional Representation (Wedge Representation): Here the structure of an organic molecule
can be represented by using solid ( ) and dashed ( ) wedges. The solid-wedge is used to
indicate a bond projecting out of the plane of paper, towards the observer. The dashed-wedge indicates
the bond projecting out of the plane of the paper and away from the observer. The broad end of the
wedge is always towards the observer. The bonds lying in plane of the paper are depicted by using a
normal line ().
E.g. methane
Acyclic or open chain or Aliphatic compounds Cyclic or ring or closed chain compounds
Benzenoid Non-benzenoid
Functional groups: Atoms or group of atoms (except hydrogen) which are bonded to carbon atoms are called
functional groups. These groups are responsible for the characteristic chemical properties of the organic
compounds. Some important functional groups, their names and name of the compounds are listed below:
Functional group Name of the group Name of compound
-OH Hydroxyl group Alcohol
-NH2 Amino group Amine
-X Halo group Halo compound
-CHO Aldehydric (formyl) group Aldehyde
-CO- or >CO Carbonyl (keto) group Ketone
-COOH Carboxyl group Carboxylic acid
-O- Oxy group Ether
-CN Cyano group Nitrile
-NO2 Nitro group Nitro compound
Homologous series: A series or group of organic compounds in which adjacent members are differed by a CH2
group is called a homologous series. The members of a homologous series are called homologues. They contain
same functional groups, have similar chemical properties and show gradation in physical properties. They can be
prepared by some general methods of preparation. E.g. for homologous series are alkanes, alkenes, alkynes,
alcohols, ethers, carboxylic acids, aldehydes, ketones, amines, halo compounds etc.
Nomenclature of organic compounds
An organic compound has two types of names Common name and IUPAC name. The common name is
based on the source or some properties. For e.g. citric acid is named so because it is found in citrus fruits and the
acid found in red ant is named formic acid since the Latin word for ant is formica.
There are two types of suffixes primary suffix and secondary suffix. Primary suffix indicates saturation or
unsaturation [for alkane the primary suffix is ane, alkene ene and for alkyne yne]. Secondary suffix indicates
the type of functional group. Some functional groups are also indicated as prefixes.
Nomenclature of branched chain alkanes:
A branch (side chain or substituent) is obtained by removing a hydrogen atom from an alkane. The
resulting group is called an alkyl group [alkane H = alkyl (i.e. word root + yl)]. The names of some common
branches are as follows:
Branch Name
-CH3 Methyl
-CH2-CH3 Ethyl
-CH2-CH2-CH3 n-propyl (normal propyl)
(CH3)2CH- isopropyl
-CH2-CH2-CH2-CH3 n-butyl
CH3-CH-CH2-CH3 sec-butyl (secondary butyl)
(CH3)2CH-CH2- isobutyl
(CH3)3C- tert-butyl (tertiary butyl)
(CH3)3C-CH2- neopentyl
Rules for naming branched chain alkanes:
IUPAC recommenced the following rules for naming a branched chain alkane.
1. Select the longest continuous chain of carbon atoms. This chain is called parent chain or root chain. If
there is more than one such chain, the chain that contains maximum number of branches is selected as
the parent chain. Also identify all the branches or substituents.
2. Number the carbon atoms of the parent chain in such a way that the branched carbon atoms get the
lowest possible numbers.
3. The names of alkyl groups attached as branches are then prefixed to the name of the parent alkane and
position of the substituents is indicated by the appropriate numbers.
4. If different alkyl groups are present, they are listed in alphabetical order. In alphabetical order, the
prefixes iso- and neo- are considered to be the part of the fundamental name of alkyl group. The prefixes
sec- and tert- are not considered to be the part of the fundamental name.
3-Ethyl-4,4-dimethylheptane
6. If the two substituents are found in equivalent positions, the lower number is given to the one coming
first in the alphabetical listing.
For example:
1,3-dimethyl butyl-
IUPAC nomenclature of compounds containing functional groups
For naming organic compounds containing functional group, the following rules are used:
1. Select the longest continuous chain containing the functional group.
2. Number the carbon atoms in such a way that the carbon to which the functional group is attached should
get the lowest possible number. In the case of functional groups containing carbon atom like CHO, -CN, -
COOH, -CONH2, -COX. -COOR etc. the numbering should start from the carbon atom of the functional
group. (i.e. carbon atom of these groups should be numbered as 1). (But for ketones, the functional group
CO- should get the lowest possible number).
3. The name of the functional group is indicated by the following suffix or prefix.
Functional group Name of compound Suffix/Prefix IUPAC name
-OH Alcohol -ol Alkanol
-NH2 Amine -amine Alkanamine
-X Halo compound Halo- Haloalkane
-CHO Aldehyde -al Alkanal
>CO Ketone -one Alkanone
-COOH Carboxylic acid -oic acid Alkanoic acid
-O- Ether Alkoxy- Alkoxy alkane
In the case of suffixes, the ending e of the corresponding alkane is replaced. E.g. IUPAC name of the
alcohol CH3-OH is methanol (methane + ol). But for nitriles, the e of the corresponding alkane is retained.
E.g. IUPAC name of CH3-CH2-CN is propanenitrile.
In the case of alkenes and alkynes, the suffix ane of the alkane is replaced by ene and yne respectively.
(i.e. word root + ene or yne). For naming alkenes or alkynes, the numbering is done in such a way that the
double or triple bond should get the lowest possible number.
Some examples are:
Compound IUPAC Name
CH3-CH2-CH=CH2 1-Butene
CH3-CH=CH-CH3 2-Butene
CH3-CH2-CC-CH3 2-Pentyne
CH3-CH2-CH2-CH2-CH2-CCH 1-Heptyne
CH3-CH2-OH Ethanol
CH3-CH2-CHOH-CH2-CH2-CH3 3-Hexanol or Hexan-3-ol or Hexanol-3
CH3-CH2-CH2-CHO 1-Butanal or Butanal
HCHO Methanal
CH3-CO-CH3 Propanone
CH3-CO-CH2-CH2-CH3 2-Pentanone or Pentan-2-one
CH3-CH2-CH2-CO-CH2-CH2-CH2-CH3 4-Octanone or Octan-4-one
HCOOH Methanoic acid
CH3-COOH Ethanoic acid
CH3-CH2-CH2-COOH 1-Butanoic acid or butanoic acid
CH3-CH2-Cl Chloroethane
CH3-CH2-CHBr-CH3 2-Bromobutane
CH2Cl-CH2-CH2-CH2-CH3 1-Chloropentane
CH3-CH2-CH2-NO2 1-Nitropropane
CH3-CH2-CH2-CN Butanenitrile
CH3-CH2-CH2-CH2-CH2-CN Hexanenitrile
CH3-O-CH3 Methoxymethane
CH3-CH2-O-CH3 Methoxyethane
CH3-CH2-CH2-O-CH2-CH3 Ethoxypropane
CH3-CH2-NH2 Ethanamine
CH3-CH2-CHNH2-CH3 2-Butanamine or Butan-2-amine
CH3-CH2-COOCH3 Methylpropanoate
CH3-CH2-COOCH2-CH3 Ethylpropanoate
Nomenclature of organic compounds containing more than one functional groups (Poly functional compounds)
Here one of the functional groups is chosen as the principal functional group and the compound is named
on that basis. The remaining functional groups (called subordinate functional groups) are named as substituents
using the appropriate prefixes. The choice of principal functional group is made on the basis of order of
preference. The order of decreasing priority for some functional groups is:
-COOH, SO3H, -COOR (R=alkyl group), -COCl, -CONH2, -CN,-CHO, >CO, -OH, -NH2, >C=C<, -CC-
The groups like alkyl (R), phenyl (C6H5-), halogens (F, Cl, Br, I), nitro (NO2), alkoxy (OR) etc. are always prefix
substituents.
For example if a compound contains both alcoholic and aldehydic groups, it is named as hydroxyalkanal,
since here aldehydic group is the principal functional group and OH group is the subordinate functional group.
The prefix names of some functional groups are as follows:
Functional group Prefix name
-OH Hydroxyl-
-NH2 Amino-
-X Halo-
-CHO Formyl-
>CO Oxo-
-COOH Carboxy-
-O- Alkoxy-
-CN Cyano-
-NO2 Nitro-
-COOR Alkoxy carbonyl-
-CONH2 Carbamoyl-
-COX Halocarbonyl-
While numbering the carbon chain, the principal functional group should get the lowest possible number.
Some examples are:
Compound IUPAC Name
CH3-CHOH-CH2-CO-CH3 4-Hydroxy-2-pentanone
CH2Cl-CH2-CHBr- CH2-CH2OH 3-Bromo-5-chloropentan-1-ol or, 3-Bromo-5-chloro-1-pentanol
CH3-CH2-CO-CH2-CH2-CHO 4-Oxohexanal
CH3-CHNH2-CH2-COOH 3-Aminobutanoic acid
CH3-CH2-CHCl-CH2-CO-CH2-COOH 5-Chloro-3-oxo-heptanoic acid
If a compound contains more than one same functional group, their number is indicated by adding the
numeral prefixes di, tri, etc. before the suffix. In such cases the full name of the parent alkane is written before
the suffix. However, the ending ne of the parent alkane is dropped in the case of compounds having more than
one double or triple bonds.
When a benzene ring is attached to an alkane with a functional group, it is considered as substituent, instead of a
parent. The name for benzene as substituent is phenyl (C6H5-, also abbreviated as Ph).
Example:
Br
3-Chloro-4-phenyl-1-butanol
2,3-Dibromo-1-phenylpentane
Isomerism
The phenomenon of existence of two or more compounds having the same molecular formula but different
structural formula or spatial arrangement of atoms is known as isomerism. Such compounds are called as
isomers. Isomers have different physical and chemical properties. Isomerism can be broadly classified into two
structural isomerism and stereo isomerism.
1. Structural isomerism
Compounds having same molecular formula but different structural formula (arrangement of atoms) are called
structural isomers and the phenomenon is called structural isomerism. There are mainly four types of structural
isomerism:
a) Chain Isomerism: Isomers differ in carbon chain or skeleton are called chain isomers and the
phenomenon is called chain isomerism.
E.g.: Pentane (C5H12)
CH3-CH2-CH2-CH2-CH3 CH3-CH-CH2-CH3 CH3
n-pentane
CH3 CH3 C CH3
isopentane CH3
(2-Methylbutane) neopentane (2,2-Dimethylpropane)
b) Position isomerism: Isomers which differ in the position of the substituent or side chain are called
position isomers and the phenomenon is called position isomerism.
E.g. : Alcohol with molecular formula C4H10O may be 1-butanol or 2-butanol
CH3-CH2-CH2-CH2-OH CH3-CHOH-CH2-CH3
1-Butanol 2-Butanol
c) Functional group isomerism: Isomers which differ in the functional group are called functional group
isomers and the phenomenon is called functional group isomerism. This isomerism is shown by alcohols
and ethers and aldehydes and ketones.
E.g. compound with the molecular formula C2H6O may be an alcohol ethanol (CH3-CH2OH) or an ether
methoxy methane (CH3-O-CH3).
d) Metamerism: Isomers which differ in the carbon chain (alkyl groups) around the functional group are
called metamers and the phenomenon is called metamerism. It is commonly shown by ethers.
E.g.: Ether with molecular formula C5H12O may be methoxybutane (CH3-O-CH2-CH2-CH2-CH3) or
ethoxypropane (CH3-CH2-O-CH2-CH2-CH3).
2. Stereo isomerism
Compounds having same molecular formula but different spatial arrangement of atoms are called
stereoisomers and the phenomenon is called stereoisomerism. They have same atom to atom bond.
There are two types of stereo isomerism Geometrical isomerism and Optical isomerism.
The diagrammatic representation of different types of isomerism is:
The species formed as a result of homolysis is called free radical. These are species which contain an odd
electron or an unpaired electron. There are three types of free radicals primary (10), secondary (20) and tertiary
(30). Their stability increases in the order 10 < 20 < 30.
Organic reactions, which take place by homolytic fission are called free radical or homopolar or nonpolar
reactions.
2. Heterolysis:
In heterolysis or heterolytic cleavage, the bond breaks in such a manner that the shared pair of electrons
remains with one of the parts.
After heterolysis, one atom has a sextet of electron and a positive charge and the other atom has an octet
of electron with atleast one lone pair and a negative charge.
A species having a carbon atom possessing sextet of electrons and a positive charge is called a
carbocation (carbonium ion). They are of three types primary, secondary and tertiary.
Carbocations are highly unstable and reactive species. Their stability increases in the order 10 < 20 < 30. The
high stability of tertiary carbocations is due to inductive effect and hyper conjugation. In carbocations, carbon
atom is in sp2 hybridisation and hence they have trigonal planar (planar triangular) shape.
If the group attached to the carbon atom is less electronegative than C, due to heterolytic cleavage, a
species with C atom containing a shared pair of electrons and negative charge is formed.
Such a species carrying a negative charge on carbon atom is called carbanion. They are also unstable and
reactive. Their stability increases in the order : 30 < 20 < 10.
The organic reactions which proceed through heterolytic bond cleavage are called ionic or heteropolar or
polar reactions.
Nucleophiles and Electrophiles
A reagent that brings an electron pair is called a nucleophile (:Nu) and the reaction is called nucleophilic
reaction. Or, nucleophiles are electron rich species attack at electron deficient centre. (The word
nucleophile means nucleus seeking).
- - - -
Example for nucleophiles are OH-, CN-, NO2 , Cl , Br , I , H2O, NH3, R-NH2 etc.
A reagent that takes away an electron pair is called an electrophile (E+) and the reaction is called
electrophilic reaction. Or, electrophiles are electron deficient species attack at electron rich centre. (The word
electrophile means electron seeking).
Example for electrophiles are carbocations (R+), -CHO, >CO etc.
Electron displacement effects in covalent bonds
In an organic molecule, the electron displacement may take place either under the influence of an atom or in
the presence of an attacking reagent. The important types of electron displacement effects are inductive effect,
electromeric effect, resonance effect and hyper conjugation.
1. Inductive effect (I effect):
It is a permanent effect arising due to the shifting of sigma electrons through a carbon chain in presence
of an atom or group of atom (having different electronegativity) attached to a carbon chain. This effect
propagates only through C C bonds. This effect decreases rapidly as the number of C atoms increases.
E.g. 1-chlorobutane CH3 CH2 CH2 CH2 Cl
Here Cl is more electronegative than C. So the electron pair in the C Cl bond is shifted towards Cl and it gets
a slight ve charge (-) and C gets a slight +ve charge (+). This carbon attracts the electron density from the
second carbon and so the 2nd carbon gets a relatively smaller positive charge (+).
Here Cl atom attracts electron towards it. So we can say that Cl atom has electron withdrawing effect or I
effect (negative inductive effect). So groups which have the ability to attract electron pairs towards it are called
I effect. Example for such groups are X (F, Cl, Br, I), nitro (-NO2), Cyano (CN-), Carboxy (-COOH), ester (-COOR),
aryloxy (-OAr) etc.
Groups which donate electron pairs towards the carbon chain are said to have +I effect or electron donating
(releasing) groups. Example for such groups are alkyl groups like methyl (-CH3), ethyl (-CH2-CH3) etc.
b) Negative Electromeric effect (-E effect): Here the pi electrons of the multiple bonds are transferred to
that atom to which the attacking reagent does not get attached.
When inductive and electromeric effects operate in opposite directions, the electromeric effect predominates.
b) Negative Resonance Effect (- R effect): Here the transfer of electrons is towards the atom or substituent
group attached to the conjugated system. E.g. R effect in nitrobenzene:
The presence of alternate single and double bonds in an open chain or cyclic system is termed as a
conjugated system.
XI Chemistry Notes By Anil Kumar K.L [HSSLiVE] Page 13
E.g. for +R effect groups: halogen, OH, OR, OCOR, NH2, NHR, NR2, NHCOR etc.
E.g. for R effect groups: COOH, CHO, >C=O, CN, NO2 etc.
4. Hyper conjugation:
It is a permanent effect. In this effect the electrons of CH bond of the alkyl group enter into partial
conjugation with the unsaturated system or with the unshared p orbital. i.e. the electrons of C H bonds get
delocalised.
e.g. ethyl cation (CH3-CH2 +)
Hyper conjugation stabilises the carbocation because electron density from the adjacent bond helps in
dispersing the positive charge. In general, the greater the number of alkyl groups attached to a positively charged
carbon atom, the greater is the hyper conjugation interaction and stabilisation of the cation.
Thus the relative stability of carbocations is in the order: (CH3)3C+ > (CH3)2CH+ > CH3-CH2+ . CH3+.
Here tertiary carbocation has 9, isopropyl has 6, ethyl carbocation has 3 and methyl carbocation has zero
hyper conjugative structures.
Hyper conjugation is also called no-bond resonance and it is also possible in alkenes and alkyl arenes.
Types of Organic reactions
Organic reactions can be classified into the following categories:
i. Substitution reactions
ii. Addition reactions
iii. Elimination reactions
iv. Rearrangement reactions
PURIFICATION OF ORGANIC COMPOUNDS
An oganic compound may contain impurities and is essential to purify it. Various methods used for the
purification of organic compounds are based on the nature of the compound and the impurity present in it.
The common techniques used for purification are as follows:
i. Sublimation
ii. Crystallisation
iii. Distillation
iv. Differential extraction and
v. Chromatography
1. Sublimation
It is the process of conversion of a solid substance directly to vapour by heating. It is used to separate
sublimable compounds from non-sublimable impurities.
In this method, the substance is placed in a sublimation apparatus and heated under vacuum. Under this
reduced pressure, the solid sublimes and condenses as a purified compound on a cooled surface. The impurities
left behind on the apparatus.
This method is used for the purification of naphthalene, iodine, camphor etc.
2. Crystallisation
This is one of the most commonly used techniques for the purification of solid organic compounds. It is based
on the difference in the solubilities of the compound and the impurities in a suitable solvent. The impure
Calculations:
Let the mass of organic compound = m g
Volume of nitrogen collected = V1 mL
Room temperature = T1 K
Volume of nitrogen at STP = P1V1 x 273 = V mL
760 T1
Where P1 and V1 are the pressure and volume of nitrogen gas.
P1= Atmospheric pressure Aqueous tension
We know that 22400 mL N2 at STP weighs 28 g.
Therefore, VmL N2 at STP weighs = 28 x V g
22400
Percentage of nitrogen = 28 x V x 100 %
22400 x m
ii) Kjeldahls method:
Here the organic compound containing nitrogen is heated with concentrated sulphuric acid. Nitrogen in the
compound gets converted to ammonium sulphate. The resulting acid mixture is then heated with excess of